Sophia Amoruso: Founder of fashion brand Nasty Gal, best-selling author of #Girlboss, and early-stage investor running Business Class and the Trust Fund venture fund.
What this episode covers
Sophia Amoruso traces her path from an unhappy San Diego/Sacramento childhood marked by parental conflict, ADHD, and depression to a rebellious, transient young adulthood of stripping, shoplifting, and odd jobs. She explains how reselling stolen and then vintage clothing on eBay grew into Nasty Gal, which scaled from $75K to a $28M profitable run rate before a $60M index Ventures raise at a $350M valuation overextended the company. The brand collapsed within roughly a year that also saw her divorce and the unflattering Netflix series 'Girlboss' premiere. She reflects on overvaluation, naivety versus convention, leadership mistakes, and self-doubt as a motivator. Now she deliberately keeps her ventures small, focusing on Business Class and early-stage investing.
The guest's own work
#Girlboss
Sophia Amoruso
“I wrote a book called girl boss and it was pink and I was like this and I looked like I knew it was up”— Sophia Amoruso
Also referenced (named, not recommended)
Evasion
“I had a friend who had written a book called evasion literally and I would go into Barnes and Noble”— Sophia Amoruso
Nasty Gal
Betty Davis
“I named it after an album by a woman named Betty Davis who had an album called Nasty Gal she was so stylish”— Sophia Amoruso
Girlboss
Netflix
“there's a Netflix series about my life and the first thing that the character says is adulthood is where dreams go to die”— Sophia Amoruso
Kajabi
Kajabi
“I'm using kajabi and drip for email and you know whatever zapier and a variety of tools that allow it to be relatively low lift”— Sophia Amoruso
Drip
Drip
“I'm using kajabi and drip for email and you know whatever zapier and a variety of tools that allow it to be relatively low lift”— Sophia Amoruso
Zapier
Zapier
“I'm using kajabi and drip for email and you know whatever zapier and a variety of tools that allow it to be relatively low lift”— Sophia Amoruso
Airtable
Airtable
“and I'm just it's right here and it's an air table the intentionality is what I find most surprising”— Sophia Amoruso
George Foreman Grill
George Foreman
“when I did get caught I had like a George Foreman grill I think a basketball organic tampons some food”— Sophia Amoruso
Adderall
“so I took Adderall this morning hmm hahaha well they will yeah just to prepare for the podcast just kidding”— Sophia Amoruso
Big reveals from this episode
- She turned down a $400 million offer to buy the company after her investor told her to ask for more.
- The first thing she ever sold online was stolen merchandise she shoplifted from big-box retailers.
- Nasty Gal went from doing $150,000 a year to $150,000 over a single lunch during its explosive growth.
- Index Ventures invested $60 million at a $350 million valuation on a business with only a $28 million run rate.
- Within about 12 months she hit the Forbes cover, her husband left, the company collapsed, and the Netflix show aired.
- She names the $350 million valuation as the nail in the coffin because it forced impossible growth expectations.
- She says her hardest day was when her husband of about a year left her after she'd made a huge personal commitment.
Worth remembering
- Both her parents worked entirely on commission, and generations of her family ran a motel rather than holding salaried jobs.
- As a child she watched her parents cut up their credit cards and file for bankruptcy in a credit counselor's office.
- She took the campus-safety host job at an art school only to get health insurance to fix a hernia she couldn't otherwise cover.
- Nasty Gal is named after a Betty Davis album; Betty Davis was briefly married to Miles Davis and 'too wild for him.'
- Nasty Gal's revenue trajectory ran $75K, then $250K, $1.1M, $6.5M, and $12M before venture capital arrived.
- After her first raise she bought a $13,000 blue slide for the office before even buying desks.
- She attended the Hoffman Process, a seven-day retreat with no phone, internet, books, or music.
- Her Business Class entrepreneurship program runs with one employee, twice-yearly launches, and 8 hours of pre-recorded video.
- She compares 'magical thinking' to Indiana Jones trusting an invisible bridge across a chasm.